
Holiday rentals in Kailua
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Top-rated holiday rentals in Kailua
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua holiday rentals
Other great holiday rentals in Kailua
Guest favourite

Guest suite in Kailua
5 out of 5 average rating, 19 reviewsLicensed Lanikai Garden Studio - Since 1985!
Guest favourite

Flat in Waikiki
5 out of 5 average rating, 11 reviewsKaimana Luxury Suite
Guest favourite

Shepherd’s hut in Kailua
4.89 out of 5 average rating, 9 reviewsThe Ohana Island Hut
Guest favourite

Flat in Waikiki
4.96 out of 5 average rating, 27 reviews29FL-Ultra Modern 1BR-Ocean View & Free Parking!

Cottage in North Shore
4.88 out of 5 average rating, 130 reviewsBest Kept Secret on Oahu! and WE ARE LICENSED!!!
Superhost

Flat in Waikiki
4.86 out of 5 average rating, 50 reviews37FL-Luxury Upscale Ocean View-Modern 1BR/Parking~
Guest favourite

Apartment in Kahuku
4.97 out of 5 average rating, 167 reviewsHonu Hideout at Turtle Bay
Top guest favourite

Flat in Waikiki
4.99 out of 5 average rating, 83 reviewsOcean View Sunset, Free Parking, Pool, 5m to Beach
Quick stats about holiday rentals in Kailua
Total rentals
360 properties
Total number of reviews
11K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Destinations to explore
- Honolulu Holiday rentals
- O‘ahu Holiday rentals
- Kauaʻi County Holiday rentals
- Island of Hawai'i Holiday rentals
- Waikiki Beach Holiday rentals
- Kailua-Kona Holiday rentals
- Kihei Holiday rentals
- Kona Holiday rentals
- Kaanapali Holiday rentals
- North Kona Holiday rentals
- Princeville Holiday rentals
- Hilo Holiday rentals
- House rentals Kailua
- Villa rentals Kailua
- Rentals with a patio Kailua
- Guest house rentals Kailua
- Rentals with a kayak Kailua
- Beachfront rentals Kailua
- Rentals with outdoor seating Kailua
- Beach apartment rentals Kailua
- Rentals with beach access Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Flat rentals Kailua
- Rentals with a hot tub Kailua
- Private suite rentals Kailua
- Rentals with pools Kailua
- Apartment rentals Kailua
- Rentals with an EV charger Kailua
- Rentals with a washing machine and dryer Kailua
- Family-friendly rentals Kailua
- Pet-friendly rentals Kailua
- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- Mālaekahana Beach
- Honolulu Zoo
- Banzai Pipeline
- Mākoa Beach
- Ala Moana Beach Park
- Kalama Beach
- Hanauma Bay
- White Plains Beach
- Kapiolani Park Beach
- Sans Souci Beach
- Kahala Hilton Beach
- Bishop Museum
- Diamond Head Beach Park
- Nimitz Beach
- Ke Iki Beach
- Pyramid Rock Beach
- Kalani Beach
- Wet 'n' Wild Hawaii
- Things to do Kailua
- Things to do Honolulu County
- Sports activities Honolulu County
- Food and drink Honolulu County
- Art and culture Honolulu County
- Entertainment Honolulu County
- Nature and outdoors Honolulu County
- Wellness Honolulu County
- Things to do Hawaii
- Entertainment Hawaii
- Wellness Hawaii
- Tours Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Art and culture Hawaii
- Food and drink Hawaii
- Nature and outdoors Hawaii
- Things to do United States
- Wellness United States
- Food and drink United States
- Tours United States
- Art and culture United States
- Entertainment United States
- Nature and outdoors United States
- Sightseeing United States
- Sports activities United States